This year might not be the best year to go all in with an investment if the sole goal is cash flow or appreciation (not personal use).In a mature market such as the smokies, I think you can reasonably arrive at a fairly narrow occupancy rate. 

This person should ideally be familiar with real estate investment strategies and flipping houses in particular.

Personally, I've bought plenty of real estate courses in the past.

I do have some personal debt that I'm working to get rid of.

In their first year, many agents  go through their personal network and get all the "low hanging fruit".

I personally have no problem driving in the rain if there was any.

I'm not familiar with vrbo and other sites- but you could at least set up your own dot com booking funnel/site & (legal- per air bnb -personally don't know?)

I don't think it has anything to do with the size of the company but the smaller guy it is just his personality. 

I personally would be careful trading options with borrowed money… seems like a risky proposition.  

This type of loan is popular as it does not require any personal income.